Across the technology companies we work with, we’ve noticed a trend: there are more Chief of Staff open roles than ever before. It’s easy to see the appeal. A Chief of Staff has the power to totally transform your company, so long as the role is effectively scoped, and the right candidate is secured and nurtured. The role can be equally amorphous to both the hiring manager and the candidates themselves. Although that’s part of the magic, the role runs a risk of being misinterpreted at best, or a total waste of resources and talent at worst.

Finding the right Chief of Staff archetype is half the battle. The harder half is bringing that hire to full potential.

After starting my career in consulting at Bain & Company, I held various positions at startups, including multiple Chief of Staff roles. I’ve tackled both low-level tasks and high-impact challenges – from manually renaming hundreds of files to setting channel strategy.

Through these Chief of Staff experiences, I’ve identified patterns around hiring philosophies, finding the best CoS archetype for any given startup and getting the most out of a CoS.

The Hiring Philosophies that Get Results

Always bet on the hustler

I took a 10–week MBA summer internship at Dame Products (Series A) because the company had strong growth, big tailwinds and a savvy leadership team. My official remit was reorganizing the Google Drive and documenting core processes. Super flashy stuff. During onboarding, I asked pointed questions about strategy and gathered as much data as possible, grounding every project in metrics and business goals in hopes of earning the opportunity to work on impactful projects. Over time, the CEO and COO trusted me with bigger challenges. By week 10, I had partnered with the President & COO to craft and present Dame’s three-year vision and execution strategy, which earned me CEO sign-off and a full-time Chief of Staff offer that I happily accepted.

Founders: prioritize candidates who are eager to grow their initial mandate by doing the work. Ask for examples of times they over-delivered on projects they owned (and dig deep on the “how”).

Expect to grow the role based on track record post-hire vs. a candidate’s current resume

When I rejoined Dame full-time seven months later, I took on typical CoS duties like investor comms and OKRs but also stepped in where needed. When our VP of Marketing left suddenly, I led our growth, wholesale, brand, and content teams—key functions for a consumer brand. Though I lacked traditional experience, with the team’s support, we launched two products, hit CAC and CPO goals, and landed Target in-store.

Founders: trust your spidey senses on candidates with the most potential, vs. those with the flashiest resumes. Lean heavily on references and backchanneling to assess this.

Don’t copy and paste your CoS search from your founder friends

My second CoS role was at FOLX Health (Series B). Despite this being my second go-around, almost everything I did at first was new to me. The company was in the middle of a business model shift without senior leadership in Finance. With the help of incredible teammates, I built a driver-based financial model that shaped pricing and product strategy, co-led a capital raise, and led strategic initiatives while staying closely involved with Finance until FOLX hired a CFO. I was able to move rapidly and in lockstep with the CEO, Liana, because she had a clear vision of the jobs to be done. She shared her 90-day plan for me before I even signed the offer. Be like Liana.

Founders: define your CoS job description specs according to what your business urgently needs – not what you think a CoS is “supposed” to do. Otherwise, you’ll be trying to fit a square peg in a round hole.

The Four Archetypes to Find the Right Chief of Staff

Before recruiting, ask yourself (and your team, your board) if now is the right time to hire. For example, if you are a deeply technical, pre-PMF, pre-seed company that is still in build mode, hold off. If you write a job description where 80% of the responsibilities are related to one specific function, hire an expert in that function instead.

If the timing is right to make the hire, determine which archetype best suits your company needs. In roughly ascending order of company size:

THE EARLY TEAM GENERALIST

The linchpin to getting your business off the ground. This CoS is an all-around business athlete that tackles everything your function-specific cofounders can’t get to.

True about your business:

• Just getting started (usually Seed or early Series A). You need to find PMF, not file taxes
• Needs someone to push the ball forward on fundamentals (finance, recruiting, business development) while you spend time doing things only you can do
• Still hiring for functional “head of” talent

True about them:

• Background: 2-3 years in fast-paced, high-pressure environments. Enough experience to be effective, with the hunger and energy to really grind.
• Best attributes:
  • Ripe for developing into a mid-level functional leader at scale
  • Energized by very early stage startup ambiguity and not above “grunt work”
• Ideal experience: banking analyst, management consultant, PE analyst/associate
• Beware of: analysts who are ineffective without a multi-month roadmap. Of all the archetypes, this one needs to be the most comfortable taking business-changing pivots in stride.

THE CONDUCTOR

The superhuman project manager. This CoS gracefully coordinates complex cross-functional projects, removes roadblocks and keeps strategic goals in focus – without being babysat.

True about your business:

• Foundation is set; in build mode (usually Series A or B)
• Strategy is largely in place, but need help quarterbacking transformational initiatives that span functions (e.g., testing into new markets, launching new products)
• “Head of” leaders are in place

True about them:

• Background: 4-6 years of experience make them skilled at influencing; leaders see them as a helpful teammate vs. a task manager.
• Best attributes:
  • Highly structured, but able to thrive in chaos
  • Proactive and intrinsically motivated
• Ideal experience: project manager or implementation consultant who has led teams
• Beware of: executors who don’t see the forest through the trees. Someone who can build and deliver on a complex project Gantt chart is great. But not if they don’t regularly pull up to ensure the project plan still serves quickly-evolving business goals.

THE FUNCTIONAL LEAD STAND-IN

The pinch hitter. This CoS effectively plugs talent and capability gaps wherever is most needed. They can step in to manage teams during lengthy executive searches while also owning long-term strategic questions outside of other executives’ scopes.

True about your business:

• Well into scaling with strong PMF, but not every C-Suite position is filled (usually Series B or C and seeing steady traction)
• Needs functional leadership who can help grow your business to the next talent level: experienced hires who have worked at scaled organizations
• Needs someone owning “strategy” besides you

True about them:

• Background: 6-8 years of highly analytical work across multiple disciplines. They can become a subject matter expert with little ramp time.
• Best attributes:
  • Confident, but has the self-awareness to know their limitations (and ask for help)
  • Strong people manager
• Ideal experience: split between management consulting/IB/VC and startups
• Beware of: folks who have never worked in startups. With rare exceptions, advisors and F500 operators have a harder time navigating the uncertainty of startups and building credibility with their functional lead peers.

THE CEO BRAIN EXTENSION

The right hand. This CoS is your proxy and is trusted to make decisions, prioritize work across teams, interface with your board and handle delicate people situations with discretion.

True about your business:

• It’s a rocketship (usually Series C+ and growing quickly). You need to concentrate your time and attention on external stakeholders more than internal operations.
• Functional leadership is generally in place, but CEO bandwidth to manage them is tight
• Because PMF is there and the strategic direction is set, CoS has a clear framework for decision-making

True about them:

• Background: Seasoned operator (10+ years – these folks are more expensive)
• Best attributes:
  • Expert at filtering information to you and other stakeholder groups
  • Strong executive presence and communication skills
• Ideal experience: GM or functional lead at scaling startup, strategic COO, senior management consultant turned operator
• Beware of: folks who aim to be a CEO themselves one day (or have already been one). This is not necessarily a disqualifier – CoS experience can be highly valuable for future founders – but you need to ensure this person is a proxy for you, not the business’s second CEO.

Getting the Most Out of Your New Chief of Staff

Even with a well-scoped role and talented hire, how you position and coach your CoS will make or break their effectiveness. The below are particularly important for strategic Chiefs of Staff:

Give them access. Chiefs of Staff are at their best when they have the ability to go deep on business challenges while also having full organizational context – including your public and non-public priorities. They should be in every leadership team meeting, have full visibility into your running to-do list, know what you really think of That Board Member’s suggestion on your last call, etc. This is how they connect dots in ways unique to the role.

Set the tone for your leadership team. Quickly give your CoS the mandate and credibility they need to execute. Redirect folks who go around your CoS, vocally support your CoS’s contributions and feedback in meetings, and hold leaders accountable when they don’t collaborate in ways they are expected to. It will feel like overkill. But if you want real leverage from your CoS, it is necessary to lead by example – or you end up doing the work yourself.

Be intentional about career pathing. It can be tempting to keep your CoS exactly where they are – particularly if they are exceptional – but the best Chiefs of Staff are rising stars who have ambition beyond the role. You should have frequent (quarterly!) professional development discussions about 1) how they are progressing toward longer-term goals, and 2) how they might achieve those goals within the company. Your CoS will have developed business context worth its weight in gold in a functional leadership position. It will pay dividends to retain that experience, and they will go above and beyond knowing you’re truly invested.

Because the Chief of Staff role is so nebulous, its impact varies. But when scoped, hired for, and nurtured well, Chiefs of Staff can be one of the most valuable roles in the org.

If you have questions on how to scope your Chief of Staff role, find the right candidates, or realize their full potential, reach out to ncoletta@baincapital.com. Aspiring Chiefs of Staff out there: very happy to connect with you, too!